ChemSusChem
ChemSusChem
5 years ago

Sustainable Production of o-Xylene from Biomass-Derived Pinacol and Acrolein

Sustainable Production of o-Xylene from Biomass-Derived Pinacol and Acrolein
Guangyi Li, Yu Cong, Xiaodong Wang, Ning Li, Yancheng Hu, Tao Zhang, Aiqin Wang
o-Xylene (OX) is a large-volume commodity chemical that is conventionally produced from fossil fuels. In this study, an efficient and sustainable two-step route is used to produce OX from biomass-derived pinacol and acrolein. In the first step, the phosphotungstic acid (HPW)-catalyzed pinacol dehydration in 1-ethyl-3-methylimidazolium chloride ([emim]Cl) selectively affords 2,3-dimethylbutadiene. The high selectivity of this reaction can be ascribed to the H-bonding interaction between Cl− and the hydroxy group of pinacol. The stabilization of the carbocation intermediate by the surrounding anion Cl− may be another reason for the high selectivity. Notably, the good reusability of the HPW/[emim]Cl system can reduce the waste output and production cost. In the second step, OX is selectively produced by a Diels–Alder reaction of 2,3-dimethylbutadiene and acrolein, followed by a Pd/C-catalyzed decarbonylation/aromatization cascade in a one-pot fashion. The sustainable two-step process efficiently produces renewable OX in 79 % overall yield. Analogously, biomass-derived crotonaldehyde and pinacol can also serve as the feedstocks for the production of 1,2,4-trimethylbenzene. Pinacol ardor: o-Xylene is produced by an efficient and sustainable two-step route from biomass-derived pinacol and acrolein. Noteworthy features of this route include a recyclable phosphotungstic acid/[emim]Cl system for selective pinacol dehydration to 2,3-dimethylbutadiene, and the one-pot production of o-xylene by a Diels–Alder reaction of 2,3-dimethylbutadiene with acrolein and subsequent decarbonylation/aromatization cascade.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/cssc.201700823

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